


The Personal Assistant

by MadLoveAndPsychoKisses



Category: Borderlands
Genre: Abusive Relationships, All The Women Want Handsome Jack, Dom/sub Undertones, Evil Corporations, F/M, Hybristophilia, Murder, Office Sex, Rough Oral Sex, Rough Sex, S&M, Threats of Violence, sexy secretary
Language: English
Status: In-Progress
Published: 2015-11-24
Updated: 2015-11-24
Packaged: 2018-05-03 03:42:06
Rating: Not Rated
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 2,953
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5275160
Author URL: https://archiveofourown.org/users/MadLoveAndPsychoKisses/pseuds/MadLoveAndPsychoKisses
Summary: <blockquote class="userstuff">
              <p>Handsome Jack gets a very eager new assistant. Her name is now Jennifer.</p>
            </blockquote>





	1. The Admission Interview

When Handsome Jack walked into his private suite at the Hyperion offices, a welcome sight greeted him: a beautiful woman lying in his bed, his silk sheets wrapped around her. He appraised her with satisfaction – curvy body, long dark hair, a sexy smile on her sensual, cherry-red lips.

“Well hel-lo,” he greeted her, raising an appreciative eyebrow as he walked to the bed. “Soooo, I’m pretty sure I know why you’re here. Unless this is some kind of really awesome assassination attempt?”

“No, Sir,” she replied demurely. “I’m the new personal assistant you requested. I was told by Personnel to come straight in and wait for you. I hope that was all right?” She swept the sheets away from her with one fluid motion, revealing her exquisite, completely naked body.

“Mm-hm,” he agreed absently, reaching out to stroke the smooth swell of her hip. Her skin was as soft and touchable as it looked. “And did they tell you to wait for me in bed, too?”

“I took the initiative to think of it, Sir. I thought you’d appreciate the introduction.” She slid one sleek thigh against the other, trailing her hands down her full breasts and along her small waist, displaying herself to best advantage.

Jack praised, “That was a good call… hm, you haven’t told me your name yet. I’m gonna call you Jennifer. Isn’t that a pretty name, Jennifer?” He loosened his tie and slipped it off, then began to undo the buttons of his jacket.

“Yes, Sir,” agreed Jennifer. Her gaze hungrily followed his fingers as they worked their way down his lean torso.

“Did you bring a copy of your resume with you today, Jennifer?” He laid his tie and jacket on the bench at the foot of the bed, then took off the Hyperion yellow t-shirt beneath it and added it to the pile.

“Of course, Sir,” she replied. “It’s on the bedside table.” She gestured towards it.

“That’s great,” Jack said warmly. “A lot of people think that because we have so much fun here, I don’t take this business seriously. Nothing could be further from the truth. Now get over here and suck my dick.”

She immediately complied, crawling over and undoing his pants with impressive speed. She ran her fingers down his shaft through the silk of his boxers, and found it already hard and ready. She wisely wasted no time in pulling down his boxers and sliding her full lips down the length of it, licking and sucking. Despite his rather impressive size, she bravely struggled to work the head of his dick down her throat.

Jack stroked her silky hair absently with one hand as he studied her resume, letting her know that her efforts were acceptable.

“Um, Jennifer, there’s a problem here,” he commented. “The name on your resume is wrong. I hope you’ll pay more attention to detail when you’re working on projects for me.”

“Sorry, Sir,” she mumbled around his dick.

“I’m sure you’ll find a way to make up for it,” he reassured her, thrusting his hips forward to secure an extra half inch down her throat. She struggled, but took it obediently. He shoved farther forward until she gagged and choked, enjoying the feel of it on his dick.

He continued, “Otherwise this looks great. I see here that your previous employers praised your excellent oral dictation skills. Now – don’t bother talking, just nod – does that mean what I think it does?” His dick deep down her throat, she gazed up at him through her eyelashes and nodded. He gave an approving groan at the sensation. “Hm, I have to say, I agree.”

He flipped to the next page. “High marks in sycophancy, good, good… you’re a proper little suck-up, aren’t you?” She moaned in response, sending vibrations down his shaft, and nodded again.

“I have a feeling this is gonna be a great position for you, pumpkin,” he said, then devoted himself to fucking her face. She eagerly serviced him, tongue swirling around his balls at the deepest part of each thrust.

Jack sighed with pleasure as he came, her skilled tongue lapping and tight little throat swallowing as his cock shuddered again and again. He withdrew from her and pulled his silk boxers back up, then just looked at her, savoring the moment.

“You do good work, kiddo,” he said, stroking her hair affectionately. “You’ve earned yourself a one week trial. Be under my desk tomorrow morning at seven a.m. sharp.” He re-dressed, allowing her to help.

“Yes, Sir,” Jennifer said, looking up at him worshipfully as she straightened his tie. “Whatever you want, Sir.”

“Of fucking course, whatever I want,” Jack chuckled. “I’m the boss, right? Also, if I wanted to, I could kill you in like, two seconds.”

She slipped her arms around his waist and pressed her cheek to his chest, snuggling against him in a way that made his cock start to swell again. “If so I would die happy, Sir, knowing that I pleased you.”

“Good, good. So hey, you know all those references I asked for? Those previous bosses of yours who were so pleased with your skills? Just wanted you to know, I’m gonna kill them all. I like what I have to be exclusive, so I’m going to be the only man alive who’s gotten head from you, okay?” He grabbed her by the chin, his fingertips digging into her jaw as he pulled her face to his for a hard, punishing kiss. Then the vaguely threatening look was replaced with his usual bright grin as he patted her on the cheek. “See you bright and early, pumpkin.”

“Yes, Sir,” Jennifer agreed, that look of worship still in her eyes. Whatever he saw fit to do - clearly, she idolized him enough that she didn't care. She was less of a problem, more convenient, better for his self-serving instincts, than any of the contrary and traitorous women he'd known. But as he smiled at her like a demon, he couldn't help but think that the struggle was part of what he liked. She was... weak. He knew that she wasn't a threat and it made her less compelling, no one to take seriously.

Nevertheless, it was not often that Jack had a temporary pleasure so suited to his desires. He’d have to send Personnel a gift basket.


	2. Working Hard

**Summary for the Chapter:**

> "Jennifer" struggles to prove herself to Handsome Jack, who appreciates her dedication.

When Jack arrived at his office the next morning, promptly at 8:00 (his usual time getting in) he was amused to see his new assistant curled up under his desk (as she must have been for an hour) looking at him with wide and lustful eyes. She was wearing a cute silk blouse through which he could clearly see she wore no bra, a knee-length pencil skirt, high heels, and stockings - very classic secretary. He approved.

Jack opened his computer and started tapping away at the virtual keyboard before looking down at her. "What are you doing under there?" he demanded. "I'm not in the mood for head." He grabbed her by the hair and yanked her into a standing position, then shoved her so she fell back onto the desk. She gasped in pain, looking at him adoringly. He slapped her across the face, hard, to make his point. The mark of his hand rose red on her cheek, claiming it; it was sexy as hell.

"Assume the position," he commanded. He was half impressed and half disappointed when she did exactly what he wanted without explaining, turning over to lean over the desk on her stomach, hiking her skirt up, and pulling her panties aside while she parted her slim thighs. The stockings were thigh-highs, attached to a tasteful garter belt. Jack stroked her bare ass lightly before playing with her pussy lips, and said in a low voice, "Hm, you have worked in an office before, haven't you?" She shuddered satisfactorily at his voice and touch.

Jack undid his pants and slipped out of the opening in his boxers, but otherwise remained dressed. The contrast between his suit and her naked flesh pleased him. He reached between her legs and slowly stroked her slit with one long finger before pushing it in, prompting her pussy to clench around it. "You're very wet," he commented, reaching to squeeze her breasts through her shirt. "Why is that?" His teasing tone showed that he knew exactly why, but she obliged him by saying it anyway.

"You're so incredibly sexy, Sir," she moaned, looking pleadingly back over her shoulder at him. "I've been hoping since I got this position that you'd fuck me. Please, I'll do whatever you want, but I really, really want to feel your cock in me, Sir." Doubt flickered through her expression - unsure whether he was intending to reward her with sex, or only tease her - and he smiled smugly at his effect on her, adding another finger before he withdrew them.

"You'll do whatever I say," Jack agreed. "Luckily for you, I want to fuck you too." He grabbed her suddenly, fingers digging deep into her hips and ass, and pulled her back onto his dick. He moaned in satisfaction as she twisted her hips to help him deeper.

He soon realized a problem, though. "Look, kiddo, you're very tight. And I'm very big. You're stuffed full, aren't you, and I'm not all the way in." She groaned her acceptance of the situation. He explained, "I'm gonna keep going, okay? And you're going to tear wide open. But that will help my cock fit into you better."

"Yes, Sir," she whimpered, getting wetter at his words. "Please... please do it." He obliged, shoving into her deep. She screamed and writhed as she tore, then shuddered and took it, thrusting her hips back against him. "Ohhhh... thank you Sir," she moaned, voice full of bliss as she took him in all the way.

"Don't worry, you'll get this a lot, pumpkin," he murmured into her ear, enjoying the feel of her clenching around his cock, so tight it was almost painful. He caressed the small of her back, and continued, "But we're gonna have to break you in, hmm? I shouldn't have to work this hard." He cut off her apology with a hand over her mouth, and felt her agonized breath against his palm as he sought out the angles to drive even deeper into her ravaged cunt. It was too much, and he groaned deeply as he started to near his climax.

Jennifer started crying out - half in pain, half in pleasure - and weathered it while he battered her wildly. He began to cum, soaking in her screams blissfully as the twitching of his cock further battered her damaged walls. "Ohhh, kid," he groaned. "Am I going to have a lot of work for you." He pulled out of her, and looked down at the quivering body draped over his desk.

"Well?" he asked, looking down at her. "Where's my fucking coffee?"

"Right away, Sir," she said hurriedly. "And I'll get something to clean up this mess." She stood, wobbling a little as balance reasserted itself, and started to brush past him.

"Wait," he demanded, grabbing her. She looked at him questioningly. "I just wanted to let you know," he said seriously, "that was a six-star performance."

"Six?" she asked, puzzled. "Why six, Sir?"

He smiled as he reached down to the surface of the desk, where six drops of blood had fallen during their violent fucking, and swirled his fingertip through one of them to make a tiny supernova. "They look like stars, don't they? Little red achievement stars."

"Yes they do, Sir," Jennifer said confidently, "I know it's true, because you say so." She reached to stroke his jaw as she kissed him on the neck.

He smiled. "I like your logic there." Then he pushed her away, and backhanded her so she flew back across the room. "Coffee, Jennifer," he reminded her coldly, and went back to work. Fantastic at sex or not, a good assistant had to know her place.


	3. Misery Loves Company

**Summary for the Chapter:**

> Handsome Jack has a bad day at the office, and tries to take it out on his endlessly obliging assistant.

It was just after lunch, and Handsome Jack was pissed. The last set of figures he'd seen said that engineering would have to be much more competitive to keep pace with that barbarian hack, Torgue. There were reports of Vault Hunters who were, infuriatingly, not dead yet. And on top of everything, a pack of skags had apparently invaded his new outdoor hot tub. The obvious thing to do was take it out on his new assistant, but how? She liked pain, at least from him, and didn't seem to fear death. He chose the next easiest way to make her suffer.

"Jennifer," he snapped as he marched into his office, "I need you to go out to the lobby and fetch something for me from the receptionist." He grabbed her blouse by the neck and ripped downwards, tearing it into rags. She barely gasped as the cloth dug into her shoulders. She stood in only her skirt, stockings and heels, the nipples on her beautiful breasts standing erect from his slightest attention. "Go like that."

"Yes, Sir," she said meekly, lowering her eyes.

"Wait," he ordered. "Take off that skirt. It's terrible. You need to dress sexy if you want to work for me." She shimmied it off, revealing a g-string that barely covered her slit.

"Is that better, Sir?" she asked seductively. It *was* pretty hot, but that wasn't what he was after now.

"Just fucking go," he sighed. She hurried off, giving him a good look at her ass, but it only stirred him a little. Why wasn't she bothered by this? She was more exposed than the cheapest whore on the block. At least he would get to punish her brutally when she returned from the lobby without his nonexistent package.

She came back in, laying a folder on his desk. "Here they are, Sir, the latest specs on the improved Hyperion line that engineering dropped off from the Opportunity branch. They're very encouraging, Sir." He was tempted to argue that it wasn't what he'd sent her for, but then she might ask for clarification, and the loyal little bitch would probably try to track down whatever he said. It was all too complicated. Instead he flipped through the pages in front of him while pondering his new assistant's fatal weakness.

...And it was obvious. It was him, wasn't it? She adored him. How fucking weak, to trust someone so completely, even someone perfect like him. She deserved to suffer for it.

"Jennifer," he instructed her, "I have something else for you to do. Take care of coordinating an orgy for tonight, would you? Only invite the most sex-crazed debutantes in my little black book. You know, kind of like you, but classier and not as desperate. It's okay to have an easy slice of pie now and again, kid - especially if you deliver it right to me - but set me up with something quality and sweet."

She looked at him with a trace of sadness, which was good, but seemed largely unfazed. "Of course, Sir. I'm sure they'll be to your liking. When would you like them to arrive?" Why wasn't she jealous? Pouting?

"You should know," he said sharply. "When I'm done with fucking work, that's when I need to relax. You keep track of my schedule, don't you?" She nodded submissively and peeked at her ledger. Jack seethed.

"Also," he continued, "I need you to fill in at a function tonight. I can't make the employee recognition ceremony. You should meet and greet the twenty men who made the most money for me last quarter and invite them all to fuck you, one after the other. If they're hesitant, tell them Handsome Jack insists."

"I'll do my very best, Sir," she agreed. How dare she not bat an eyelid, the shameless whore? She was his now. He wanted to strangle her, but had an unpleasant vision of her sitting still and taking that too.

"I want to carve you open and finger paint with your blood while I fuck the new hole, you stupid bitch," Jack growled, and was further infuriated to see the look of lust in her eyes.

"What the fuck is wrong with you?" he demanded. "I keep trying, but nothing bothers you."

A stricken look crossed her face as she made sense of it. "I... I can't give you what you want?" she asked slowly. "I..." Her lip trembled, and tears welled to her eyes. "Oh, Sir!" she cried, and flung herself down at his feet as she wept brokenly. She was far lower than she could have been if he had tortured her in any conventional way.

Jack was speechless for a rare moment. Then he gathered her up into his arms and held her tight, making soothing noises. "Shhh. It's okay, I'm not really mad, I was just joking around. You're a good girl."

She looked up at him, her tear-streaked face full of gratitude. "Do you mean it?"

"Yes," he reassured her. "You are an absolute delight, Jennifer. I am so pleased to have you working for me." He kissed her temple and cuddled her, feeling her relax.

"You know," he confided in a lower voice, "you're going to have to do a LOT to keep me happy with you. But you're up for a challenge, aren't you, Jennifer?" She nodded, her head moving against his chest almost imperceptibly. 

"You're the best assistant I've ever had," he said soothingly, mind already spinning with impossible and soul destroying tasks. Handsome Jack didn't rise to the top of the corporate world for nothing; he liked a challenge himself.


End file.
